Efficient synthesis and biological evaluation of new benzopyran-annulated pyrano[2,3-c]pyrazole derivatives

被引：8

作者：

Labana, Balvantsingh M. ^{[1
]}

Brahmbhatt, Gaurangkumar C. ^{[1
]}

Sutariya, Tushar R. ^{[1
]}

Parmar, Narsidas J. ^{[1
]}

Padron, Jose M. ^{[2
]}

Kant, Rajni ^{[3
]}

Gupta, Vivek K. ^{[3
]}

机构：

[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India

[2] Univ La Laguna, IUBO AG, Ctr Invest Biomed Canarias CIBICAN, BioLab, C Astrofis Francisco Sanchez 2, San Cristobal la Laguna 38206, Spain

[3] Univ Jammu, Postgrad Dept Phys, Jammu 180006, India

来源：

MOLECULAR DIVERSITY | 2017年 / 21卷 / 02期

关键词：

DKHDA reaction; Ketone-based DKHDA substrates; Benzopyran; Pyrano[2,3-c]pyrazole; Antiproliferative activity;

D O I：

10.1007/s11030-017-9734-y

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A one-pot method has been described to synthesize benzopyran-annulated pyrano[2,3-c] pyrazoles, effectively by combining O-alkenyloxy/alkynyloxy-acetophenones with various pyrazolones in triethylammonium acetate (TEAA) under microwave irradiation. While combination of O-allyloxy-or O-prenyloxy-acetophenones with pyrazolones occurred efficiently, that of O-propargyloxy-acetophenones was found effective in the presence of ZnO catalyst, via a domino Knoevenagel-hetero-Diels-Alder (DKHDA) reaction. Aminobenzopyran frameworks were also synthesized, after nitro-containing products were reduced in tandem with iron(II) in an acidic medium. The in vitro antiproliferative activity of these compounds was measured and discussed against gram-positive, gram-negative and M. tuberculosis bacteria, fungi, and various representative human solid tumor cell lines, in addition to their ferric reducing antioxidant capability.

引用

页码：339 / 354

页数：16

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